This study attempts to derive adaptive metacognitive self-regulatory processes by extending Wells and Matthews' (1994, 1996) and Wells' (2000) metacognitive model of psychological and emotional disorders and blending it with adaptive assets within a positive psychology framework. The assumption of this study is that adaptive self-regulation, specifically in the light of challenge, unpredictability or ambiguity, should contribute to emotional equilibrium, psychological well-being and - in the long term - to life satisfaction and other facets of quality of life. The current economic crisis with increased job insecurity necessitates even more pronounced adaptations to challenge and change. Thirteen interviewees were recruited by purposive sampling based on their assumed positive metacognitions and adaptive assets. The participants were high profile executives and known to the researcher due to work-related contacts. A semi-structured interview schedule using positive metacognitive priming techniques was applied to elicit interviewees' recall of functional self-regulatory processes and also their accounts of adaptive personality factors (assets) when facing mid- to long-term challenging tasks or projects. The verbatim interview transcripts were analyzed by employing Hayes' (1997) Theory-led Thematic Analysis with focus on =keyness' rather than prevalence of themes or categories. In an attempt to discover novel themes, potentially emerging above and beyond the framework of the interview schedule, the Theory-led Thematic Analysis was blended with Glaser and Strauss' (1967) Grounded Theory approach. Results showed that the majority of participants used adaptive metacognitive modes of information processing (Wells & Matthews, 1994, 1996) preventing potentially maladaptive metacognitive processing. Beyond Wells and Matthews' framework participants also accounted for adaptive metaemotional processes, e.g. mindfulness, frustration tolerance and refraining from inappropriate overreaction. In terms of personality assets, resilience (Masten & Reed, 2005) emerged as a key factor or theme with the two subordinate themes of agency and communion (Wiggins & Broughton, 1985). A plethora of additional more specific adaptive constructs were identified, e.g. persistence, optimism, and the ability to experience positive emotions in the midst of high challenge (Folkman & Moscowitz, 2000). The study's overall results supported challenge models of resilience. With regard to the duration of the challenge scenarios the following distinction resulted: Very long-term challenge scenarios required a higher degree of resilience-related factors, whereas metacognitive and meta-emotional self-regulation was crucial when challenge was of shortto mid-term nature. Results can potentially inform intervention programs to effectively cope with and functionally adapt to challenge and unpredictability in occupational and other life domains. The study provided the framework for the recently developed and validated Positive Metacognitions and Positive Meta-Emotions Questionnaire (PMCEQ, Beer & Moneta, 2010). The utlization of the PMCEQ in turn provided empirical evidence in quantitative follow-up studies that functional metacognitions and adaptive meta-emotions prevent maladaptive coping, foster adaptive coping and decrease stress perception, anxiety and depression (Beer & Moneta, 2011).